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Kasey Kesselring has built Montverde Academy into an academic and athletic powerhouse

Around 3 o’clock on a September afternoon, students in polos and khakis trickle out of whitewashed buildings on Montverde Academy’s campus in southern Lake County. Some scatter to the basketball courts, soccer fields and batting cages for practice. The girls golf and volleyball teams are headed to Orlando to play against Bishop Moore Catholic. With 1,300 students ranging from pre-K through high school, the prep school’s population nearly matches that of the tiny Central Florida town where it’s situated — Montverde had 1,675 residents as of 2018, according to the U.S. Census Bureau.

The 125-acre campus wasn’t always bustling. When Kasey Kesselring arrived as the headmaster in the fall of 1999, the school had only 103 full-time students — most of whom lived in dorms — and it lacked the kind of rigorous curriculum typical at a college prep school. There were no honors programs, no Advanced Placement courses and little in the way of extracurricular activities. In those days, Montverde — pronounced Montverd — had a reputation as a way station for Holden Caulfield types who needed a dose of discipline to get through their teenage years.

Kesselring, then 31 and new to the headmaster role, believed the school, founded in 1912, was ripe for transformation, but he needed a way to jump-start enrollment. “I really wanted to continue to strengthen the programs of the school and to really do that, the data sort of indicates that minimally, you’d need to have a core population of between 400 to 450 students,” Kesselring recalls. That’s when he started eyeing the local community.

Upscale housing developments were beginning to crop up in Clermont, Minneola, Groveland, and other nearby parts of South Lake and West Orange counties, and the public schools were having trouble keeping up with the growing student population. “A lot of families were moving into the area,” recalls Kesselring, who suggested to his board of directors that they appeal to some of the new residents with young children and branch out to serve more day students. They signed off on his plan, and in 2003, Montverde added elementary and middle school divisions. By the end of the year, every seat was filled, and within a couple years, Montverde was expanding the programs.

Today, approximately 1,000 day students attend Montverde Academy. Tuition ranges from $8,850 to $18,350 a year, depending on the grade level. The boarding school — which costs $52,000 a year — is also at capacity with 300 students, most of whom come from abroad. Students enjoy a 17:1 student-faculty ratio and a solid college-prep education: Montverde’s academic bragging rights include a 100% college acceptance rate, and student performance on Advanced Placement exams is better than state and national averages, with 85% of the students earning qualifying scores of 3 or higher on the tests. Seventy percent of Montverde’s teachers have advanced degrees.

Amid its growth, the school also spruced up its campus, adding $70 million in infrastructure improvements — including a $1.5 million fine arts center, a $6.5-million athletic facility and additional classroom and administrative space. It broke ground on a 40,000-sq.- ft. middle school last year.

Tuition alone hasn’t paid for all of Montverde’s capital improvements. It used tax-exempt bonds to finance the athletic center, servicing the debt with returns on the school’s endowment — and it’s turned to donors to fund smaller projects, including a 205,000-sq.-ft. expansion of the Duncan Student Center, updates to classrooms and new athletic fields. With a donation from Orlando Health/South Lake Hospital, for instance, the school in 2018 was able to install an eco-friendly turf soccer field within its 15-acre sports complex.

The sports factor

Nothing has put Montverde Academy on the map more than its sports programs. The school’s basketball team has won five of the last eight high school national championships — the most that any high school has won in a decade — and two dozen players from the school have gone on to play professionally, either in the NBA or on international teams. Alumni include Ben Simmons, who plays for the Philadelphia 76ers, and RJ Barrett, a rookie with the New York Knicks.

Montverde’s boys varsity soccer team, meanwhile, has won eight of the last 10 national championships, and the Lady Eagles varsity soccer team finished its 2020 season with a No. 1 national ranking after winning state championships in 2018 and 2019. The school also operates three sports academies — for basketball, soccer and tennis — that allow students to spend half their day focused on academics and the other half improving their game.

Mike Potempa, who joined Montverde as head coach of the boys varsity soccer team in 2010 after coaching at Clemson University, marvels at the change he’s witnessed over the past decade. “I can tell you, in my first years here, I would go to Publix down the road and people would see Montverde Academy on my polo shirt and they’d say, ‘Where is that school?’ — and it’s literally five minutes down the road. Now it’s a global brand.”

A ‘conveyor belt’ of talent

Montverde was founded in 1912 by a Kentucky transplant named Henry Carpenter with the aim of providing “mental, moral and industrial training” to the “worthy poor,” according to a 1914 school catalog. The Montverde Industrial School, as it was called back then, consisted of a two-room classroom and a church. Dorms were added later, along with broom and canning factories where students worked to earn their keep. Agricultural operations helped to feed the student body. In the 1930s, as the school shifted its focus toward academics, it dropped the word industrial and became simply the Montverde School, then, in the 1960s, Montverde Academy.

The institution also began to attract students from other countries whose parents saw prep school as a pathway for their children to gain admission to U.S. universities — either via academics or sports. That trend has intensified over the last couple of decades as American parents’ interest in sending their children to boarding schools waned. Today, full-paying international students have become a financial lifeline for many private schools. At Montverde, dozens of students come from 90 countries outside the U.S., including China, Brazil, Japan, Russia and Canada. The prep school also operates a tiny sister campus in Shanghai.

The cultivation of athletic success has been key to Montverde’s growth. Two decades ago, the school offered few sports and racked up few victories, outside of soccer. “We had always attracted kids from South America because of our proximity here in Florida,” Kesselring says. “When they came here, they were already well developed soccer players, so we always did quite well in soccer, but the rest of the sports, we didn’t do very well, nor did we have many of them.”

Kesselring’s hiring of Kevin Sutton as basketball coach in 2003 changed that. Sutton, who’d coached at several prep schools in Maryland, led the Montverde Eagles to a 21-2 record during his first season. By 2007, the undefeated team was the HoopsUSA.com national champion. The Orlando Sentinel hailed Sutton for creating “one of the nation’s swiftestrising, and best, high-school programs.” Three years later, the Eagles earned an invitation to play in the National High School Invitational.

The Sutton era came to a sudden close in 2011 when Kesselring let him go. His replacement: Kevin Boyle, a legendary high school basketball coach who had led New Jersey’s St. Patrick High School to five state championship titles and produced a slew of college ballers and NBA stars. Kesselring and Boyle had met several years earlier at a tournament in Texas. By 2011, St. Patrick, like many Catholic schools, was struggling to keep its doors open amid declining enrollment. Boyle says Kesselring was “looking to go in a different direction with basketball at the school.”

The fast-talking New Jerseyite, who played guard at Seton Hall, says he found the location enticing — “my wife, Kelly, and I always loved Florida and always took our kids to Disney World” — and was impressed by the school’s academic reputation and culture. He headed to Montverde, knowing “confidently” that with its resources he “could possibly make them the best high school in America.”

In Boyle’s first season, ESPN ranked Montverde 12th in the nation. In the years since, the prep school has won five national titles and become, in the words of an ESPN announcer, a “conveyor belt of future NBA talent.” Over his tenure, Boyle has coached No. 1 NBA pick Ben Simmons, a 6-foot-10-inch phenom from Australia; No. 2 pick D’Angelo Russell, now an All Star point guard with the Minnesota Timberwolves; and No. 3 picks RJ Barrett and Joel Embiid, a 7-foot Cameroonian who now plays with Simmons for the Philadelphia 76ers. Last season, Boyle led the Eagles to a 25-0 record, and USA Today’s latest 2021 mock NBA draft predicts that four recent Montverde alums — Cade Cunningham, Scottie Barnes, Moses Moody and Michael Devoe — will be first-round picks in next year’s draft. “Personally, I’ve had more guys who’ve played for me picked one, two or three in the NBA draft of any college, except Duke, in the last 10 years,” he says.

Given its caliber, Montverde basketball gets plenty of attention and resources. On game night, supporters come from as far away as the Villages, some 40 miles away, and fill up tide 1,500 seats in the “Nest” gymnasium, officially known as the EdgeCenter for Sportsmanship and Wellness. Members of the school’s Athletic Booster Club (big donors) get a bird’s-eye view from cushioned seats on a balcony known as “the perch” that’s stocked with food and drinks. The building’s 5,000-sq.-ft. fitness center features an indoor turf training area and a host of exercise machines.

The athletic training room is equipped with an array of medical gadgetry — including a Game Ready Med4 Elite unit that provides alternative heat and ice therapy to reduce pain and swelling and two portable GR Pro 2.1 units.

Potempa says Montverde’s sports investment reflects Kesselring’s business acumen. “He understands the world we live in, and he’ll tell you this — he doesn’t necessarily agree with it, but he understands it — why do people know about Notre Dame? It’s because of football. Why do people know about Duke? It’s because of basketball,” Potempa says. “We view our athletic program as an extension of our marketing program, so we’ve invested in it heavily.”

Fielding controversy

Not surprisingly, Montverde’s winning ways have also provoked occasional questions and controversy about how the school gets all its talent.

In 2007, the Florida High School Athletic Association began investigating the prep school after the Orlando Sentinel ran a story about how the school had raised the profile of its baseball team with 17 players from Puerto Rico. The FHSAA concluded the school violated regulations in 2005, when its baseball coach and an admissions director traveled to Puerto Rico, held an admissions open house at a hotel and attended a two-day camp where they met and observed baseball players — including five who eventually enrolled at Montverde.

The school ended up receiving a reprimand, a $10,000 fine and was placed on a two-year probation, during which it was not allowed to participate in state playoffs in 2008 or 2009. The Montverde Eagles were also limited to 20 regular season games and forbidden from playing teams from outside of the state or the country. Kesselring didn’t fight or the appeal the decision.

Today, the school competes as an independent member of the FHSAA. Under the arrangement, Montverde doesn’t compete in FHSAA state playoffs in baseball, basketball, soccer or tennis. Montverde Academy spokeswoman Andrea Colby says it has nothing to do with the baseball controversy, but that given the “elite” nature of Montverde’s sports programs, it would give Montverde an unfair advantage over other schools.

Montverde coaches, meanwhile, insist they don’t have to recruit because the school’s reputation is well known: “I get a minimum of five calls a week, from somebody, somewhere, all over the world that has questions and wants to come here. It kind of self-recruits,” says Boyle.

While Montverde does offer “qualified students” financial aid awards based on financial needs and availability of funds, it does not offer athletic or merit-based scholarships. Its latest available financial statements indicate the non-profit school doesn’t hand out a lot of discounts. It collected $27.2 million in tuition, room and board in 2017, according to its IRS filings for that year.

Potempa, the soccer coach, says the school’s academies are what really opened up the international floodgates at Montverde. “When I first arrived, there was just one (soccer) team with 20 kids,” Potempa says. “I told the headmaster, ‘Look, we can do something very interesting to attract more kids from around the world, diversify our market globally, if we can take any kid who is interested in learning soccer, not just your elite level ones.’ ”

Kesselring liked the idea and in 2013, Montverde opened the Soccer Institute at Montverde Academy (SIMA) with about four dozen students, split 70/30 between boarding and day students. Last year, the program had 204 students — with about two-thirds of them coming from abroad. SIMA students range in age from 11 to 19 and play on 10 teams, depending on their ability level.

“Obviously, when you have a soccer program, you can go anywhere in the world, speak the sport and people are going to be interested in coming to the United States, learning English and getting a private school education,” Potempa says. “That was really a very powerful concept ... (that) can attract pretty much people from all walks of life from around the world through sport.”

Montverde replicated the model with its Center for Basketball Development in 2014, and again with the arts, launching music and theater conservatories that today serve about 50 students. Dean Bell, Montverde’s director of arts, says the bulk of the kids in the award-winning conservatory programs are aiming for college scholarships and professional careers on stage. “A lot of the kids are looking to make it to Broadway,” he says.

Whatever their passion, students at Montverde are expected to put academics first — and that, says Kesselring, is what sets Montverde apart from other prep sports powerhouses. “Our emphasis is still very much cued and centered on the academic component,” he says. “That’s the paramount piece. If you’re going to come here, you’re going to have to be prepared, dedicated and committed to a college preparatory education, regardless of what your interests may be outside this.”

Rick Ellis, the school’s director of college guidance and a former director of admission of Stetson University, says, “We have some of the best athletes in the country, but we’re not just an athlete breeding ground,” he says. “The goal of any independent school is to prepare students for college.” And colleges and universities are keen on Montverde: More than 100 descend on the prep school to recruit each year.

Kesselring says he’s always been “mindful” of not letting Montverde’s sports success overshadow the school “because there are so many other good things” happening there. “It’s easy to lei: those types of things begin to direct you as an institution — for them to become too much of a focal point, where those successes are so paramount to certain segments of the school population that we begin to run the risk of losing ourselves in that.”

Kasey Kesselring, 52

Head of School, Montverde Academy

Education: Bachelor’s degree, Dickinson College (1990); master’s degree, Middle Tennessee State University (1997); doctorate in education, California Coast University (2011)

Experience: Assistant headmaster, the Webb School (Bell Buckle, Tenn.)

Family: His wife, Maureen, is director of learning support systems at Montverde Academy. The couple have two grown children.

Outside of Work: “We’ve always maintained a connection with Tennessee. We have a farm there, so if I’m not here, we’re probably at the farm doing innocuous things: Mowing, bush-hogging, cleaning. Things of that sort that I just enjoy.”

Looking Ahead: “I don’t want to personally get into a place that just because you’ve been there for 20-plus years, you’re just kind of steering the boat, trying not to hit any icebergs. Really, what I want to do is continue charting new courses.”

Star Track

Ben Simmons could have gone anywhere to play basketball, but at age 16, the Australian basketball prodigy chose Montverde Academy outside Orlando. In the 2016 Showtime documentary One and Done, his father, Dave Simmons, said it was the methods of Kevin Boyle — a gritty, intense and in-your-face coach — that sold them on the program. “I did my homework, looked at Kevin Boyle on tape. He made sense in what he was saying, some of his coaching. In fact, I thought he was similar to me,” remarked Simmons, who played 13 seasons in the Australian National Basketball League and coached for two years with a team down under. The younger Simmons, who now plays for the Philadelphia 76ers, told ESPN in a 2020 interview that Boyle is his all-time favorite coach. The two still text regularly.

Drawing Factors

On a typical day at Montverde Academy, Bradley Peterson gets up at 6:30, tidies up his room to pass “mandatory room check,” grabs some breakfast in the dining hall and heads to class. He’s taking two Advanced Placement classes this year — AP European History and AP Biology, which he figures will help him with a potential career one day as a forensic investigator. But his real passion is lacrosse. The 18-year-old goalie with a 4.2 GPA says it’s the main reason he made the switch to the prep school three years ago. “All the local high schools around me didn’t offer the sport that I wanted to play,” he says. While Peterson’s family lives in Tavares, he moved on campus this year to serve as a “prefect,” mentoring fellow boarding students and serving as a liaison between them and school administrators. He says he doesn’t miss the 45-minute drive to campus and has managed to pick up a little bit of French and Portuguese from his international classmates. He’s also discovered that a pick-up game of soccer can be a great ice breaker. “It might be a struggle at first to understand one another, but once you get past that point, you can make some pretty cool relationships.”

Athletic Champs

Hoop Feats

  • Winner of five national championship titles for high school basketball (2013, 2014, 2015, 2018, 2020)
  • Seven NBA draft picks since 2005
  • More than 100 college basketball commitments (NCAA I, II, III, NAIA)

Boys Soccer Success

  • Eight national championships in the last decade
  • 300-plus graduates have gone on to play college soccer on scholarship
  • 49 have signed professional contracts

Girls Soccer Success

  • Won back-to-back state championships in 2018 and 2019
  • Ranked No. 1 nationally by Top Drawer Soccer for the 2019-20 season
  • Jody Brown, a leading goal scorer from Jamaica who graduated last year and is playing Division 1 soccer at Florida State University, competed in the 2018 Concacaf Tournament, helping her native country qualify for the FIFA Women’s World Cup.

Other Accolades

  • Montverde’s powerlifting team has won the World Association of Benchers and Deadlifters world championship in 2015, 2016 and 2017.
  • The boys tennis team won back-to-back FHSAA state titles in 2017 and 2018 and won its first national championship title in 2019 at the DecoTurf High School Tennis Team Championships in Chattanooga, Tenn.
  • A magnet for international students, the prep school also operates a small sister campus in the suburbs of Shanghai, China, where classes are taught in English. Students who graduate earn a Montverde Academy diploma; many go on to attend colleges and universities in the United States.


Read more in Florida Trend's November 2020 issue.
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